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| CAS No.: | 63-74-1 |
|---|---|
| Name: | Sulfanilamide |
| Article Data: | 103 |
| Molecular Structure: | |
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|
|
| Formula: | C6H8N2O2S |
| Molecular Weight: | 172.208 |
| Synonyms: | Sulfanilamide (SN);Sulfanilamide(8CI);(4-(Aminosulfonyl)phenyl)amine;4-(Aminosulfonyl)aniline;4-Aminobenzenesulfonamide;4-Aminophenylsulfonamide;A-349;Albosal;Ambeside;Antistrept;Astreptine;Bactesid;Deseptyl;Dipron;Ergaseptine;Erysipan;Fourneau 1162;Gombardol;Infepan;NSC 7618;Neococcyl;Orgaseptine;PABS;Prontosil white;PronzinAlbum;Proseptine;Proseptol;Pysococcine;Ro 1-3354;Rubiazol A;Sanamid;Septamide Album;Septanilam;Septinal;Septoplex;Septoplix;Stramid;Strepamide;Strepsan;Streptasol;Streptocid;Streptocid album;Streptocide (white);Streptoclase;Strepton;Streptopan;Streptosil;Sulfamidyl;Sulfana;Sulfanalone;Sulfanidyl;Sulfanil;Sulfanilamide Vaginal Cream;Sulfonamide;Sulfonylamide;Sulphanilamide;Tolder;Whitestreptocide;p-Aminophenylsulfonamide;p-Anilinesulfonamide;p-Sulfamoylaniline;Sulfanilamide; |
| EINECS: | 200-563-4 |
| Density: | 1.427 g/cm3 |
| Melting Point: | 164-167 °C |
| Boiling Point: | 400.5 °C at 760 mmHg |
| Flash Point: | 196 °C |
| Solubility: | 7.5 g/L at 25 °C |
| Appearance: | White to almost white crystalline powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 40 |
| Safety: | 24/25-36-22 |
| PSA: | 94.56000 |
| LogP: | 2.27850 |
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- 914458-26-7[5-(2-fluorophenyl)-1-pentyl-1H-pyrrol-3-yl]-1-naphthalenyl-Methanone
- 894852-01-87-BROMO-2,2-DIMETHYL-2H-PYRIDO[3,2-B][1,4]OXAZIN-3(4H)-ONE
| Conditions | Yield |
|---|---|
| With hydrogen In methanol; ethyl acetate under 760.051 Torr; for 4h; Heating; Flow reactor; Green chemistry; | 99% |
| With maghemite-palladium nanocomposite; hydrogen In ethanol; ethyl acetate at 30℃; for 0.0125h; | 98% |
| With sodium tetrahydroborate In water at 20℃; for 0.5h; Green chemistry; | 98% |
- 36326-86-0
4-azidobenzenesulfonamide
- 63-74-1
sulfanilamide
| Conditions | Yield |
|---|---|
| With D-glucose; potassium hydroxide In water at 85℃; for 0.0833333h; Green chemistry; chemoselective reaction; | 99% |
- 14860-69-6
(p-aminobenzene)sulfonyl azide
- 63-74-1
sulfanilamide
| Conditions | Yield |
|---|---|
| With C24H21CuN3O3; sodium L-ascorbate In water; tert-butyl alcohol at 80℃; for 6h; Inert atmosphere; | 98% |
| With C27H34ClN2ORu(1+)*Cl(1-); sodium formate In aq. phosphate buffer at 37℃; for 24h; pH=7.4; |
| Conditions | Yield |
|---|---|
| Stage #1: chlorobenzene With chlorosulfonic acid; ammonium chloride In 1,2-dichloro-ethane at 55℃; for 4h; Stage #2: With ammonia In water; 1,2-dichloro-ethane at 15 - 40℃; for 2h; Stage #3: With copper(l) iodide In water; 1,2-dichloro-ethane at 160℃; for 12h; Reagent/catalyst; Temperature; | 97.5% |
- 57-67-0
1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene
A
- 722-27-0
bis(4-aminophenyl)disulfide
B
- 63-74-1
sulfanilamide
C
- 62-53-3
aniline
D
- 121-57-3
4-aminobenzene sulfonic acid
| Conditions | Yield |
|---|---|
| In methanol for 76h; Product distribution; Mechanism; Irradiation; λ=254 nm; | A n/a B 4.4% C 95.1% D 2.7% |
- 352542-64-4
tert-butyl (4-sulfamoylphenyl)carbamate
- 63-74-1
sulfanilamide
| Conditions | Yield |
|---|---|
| With H-β zeolite In dichloromethane for 10h; Heating; | 91% |
| Conditions | Yield |
|---|---|
| Stage #1: Acetanilid With chlorosulfonic acid; thionyl chloride; phosphorus pentoxide In tetrachloromethane at 60 - 90℃; Stage #2: With ammonia In tetrachloromethane at 50℃; for 3h; | 86.98% |
| Multi-step reaction with 3 steps 1.1: chlorosulfonic acid / 55 h / 40 °C 1.2: 3 h / 65 °C 2.1: ammonium hydroxide / 1,2-dichloro-ethane / 2.5 h / 15 - 40 °C / Large scale 3.1: sodium hydroxide / 3 h / 90 °C / Large scale View Scheme |
| Conditions | Yield |
|---|---|
| With ammonia; dihydrogen peroxide In water; tert-butyl alcohol at 75℃; for 2h; Reagent/catalyst; Temperature; Molecular sieve; | 82.3% |
- 2858-20-0
5-chloro-2,6-dimethyl-pyrimidin-4-ylamine
- 121-60-8
p-acetylaminobenzenesulfonyl chloride
A
- 54951-54-1
N-[4-(dimethylamino-4-ylsulfonyl)phenyl]acetamide
B
- 63-74-1
sulfanilamide
C
- 4015-18-3
Sulfaclomid
D
- 84729-42-0
C22H22ClN5O6S2
E
- 4049-04-1
4-(4'-Acetylaminobenzensulfonyl)amino-5-chlor-2,6-dimethylpyrimidin
| Conditions | Yield |
|---|---|
| With trimethylamine In dichloromethane at 33 - 40℃; for 10h; Mechanism; Product distribution; further amines; | A n/a B n/a C n/a D 70% E n/a |
| Conditions | Yield |
|---|---|
| With hydrogenchloride; water In ethanol for 1h; Reflux; | 68% |
| With hydrogenchloride | |
| With sodium hydroxide |
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Consensus Reports
Specification
The IUPAC name of Sulfanilamide is 4-aminobenzenesulfonamide. With the CAS registry number 63-74-1 and EINECS 200-563-4, it is also named as Benzenesulfonamide, p-amino-. The product's categories are Sulfonamides (Antibiotics for Research and Experimental Use); Antibiotics for Research and Experimental Use; Biochemistry. It is white to almost white crystalline powder which is alightly soluble in cold water, ethanol, methanol, ether and acetone, soluble in boiling water, glycerol, hydrochloric acid, potassium hydroxide and sodium hydroxide solution, insoluble in chloroform, ether, benzene or petroleum ether. As an antibiotic, this chemical functions by competitively inhibiting (ie, by acting as a substrate analogue) enzymatic reactions involving para-aminobenzoic acid (PABA). Additionally, it should be sealed in the container and stored in the cool and dry place.
The other characteristics of Sulfanilamide can be summarized as:
(1)ACD/LogP: -0.72; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.72; (4)ACD/LogD (pH 7.4): -0.72; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 9.66; (8)ACD/KOC (pH 7.4): 9.66; (9)#H bond acceptors: 4; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 49 Å2; (13)Index of Refraction: 1.627; (14)Molar Refractivity: 42.8 cm3; (15)Molar Volume: 120.6 cm3; (16)Surface Tension: 63.7 dyne/cm; (17)Enthalpy of Vaporization: 65.13 kJ/mol; (18)Vapour Pressure: 1.27E-06 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 172.030648; (21)MonoIsotopic Mass: 172.030648; (22)Topological Polar Surface Area: 94.6; (23)Heavy Atom Count: 11; (24)Complexity: 211.
Preparation of Sulfanilamide:
It can be obtained by chlorosulfonation, amination, hydrolysis and neutralization of acetanilide.
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Uses of Sulfanilamide:
It is not only used as reagent in the determination of nitrite, but also used in the pharmaceutical industry. It is also the major raw material in the production of sulfonamides drug. What's more, it is used in organic synthesis. For example, it can react with furfural to get 4-(2-formyl-pyrrol-1-yl)-benzenesulfonic acid amide. This reaction needs reagent 2N-HCl and solvent ethanol by heating. The reaction time is 5 hours. The yield is 41%.
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When you are using Sulfanilamide, please be cautious about it as the following:
It has limited evidence of a carcinogenic effect. So people should not breathe dust and avoid contact with skin and eyes. If you want to contact this product, you must wear suitable protective clothing.
People can use the following data to convert to the molecule structure.
1. SMILES:O=S(=O)(c1ccc(N)cc1)N
2. InChI:InChI=1/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)
3. InChIKey:FDDDEECHVMSUSB-UHFFFAOYAI
The following are the toxicity data of Sulfanilamide:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LD50 | oral | 2gm/kg (2000mg/kg) | Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 1079, 1966. | |
| guinea pig | LD50 | oral | 3130mg/kg (3130mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 82, Pg. 86, 1944. | |
| mouse | LD50 | intraperitoneal | 5mg/kg (5mg/kg) | Antibiotics Annual. Vol. 5, Pg. 886, 1957/1958. | |
| mouse | LD50 | intravenous | 500mg/kg (500mg/kg) | Antibiotics Annual. Vol. 5, Pg. 972, 1957/1958. | |
| mouse | LD50 | oral | 3gm/kg (3000mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 48, Pg. 336, 1952. | |
| mouse | LD50 | subcutaneous | 2900mg/kg (2900mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 213, 1955. | |
| rabbit | LD50 | oral | 1300mg/kg (1300mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 31(3), Pg. 11, 1966. | |
| rat | LD50 | intravenous | 1400mg/kg (1400mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 211, Pg. 367, 1950. | |
| rat | LD50 | oral | 3900mg/kg (3900mg/kg) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1072, 1986. |
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